Chemistry of organometallic complex enables to readily construct new bonds between carbon and carbon or carbon and hetero atom, and is widely used in various chemical fields including drug discovery and organic synthesis. The present inventors have devoted adequate effort to development of novel reactions and synthesis of bioactive compounds using organometallic complexes such as of ruthenium, palladium, and rare earth metal ytterbium, and have reported findings.
Reactions using an organometallic complex however have the major issue of removal of trace metals remaining in a reaction product after the reaction, as well as a problem in stability of the organometallic complex. The issue should be solved urgently particularly in the field of fine chemical for producing pharmaceuticals and electronic components, because the trace metals are harmful to humans and impair expected product's function (see, for example, Non-Patent Document 1). In addition, considering to the recent high social demand for the development of environment-conscious process, use of organometallic complexes in industrial scale has many problems in efficiency and recovery of a metal in a catalyst used and treatment of waste solution containing a metal, as well as the issue of removal of trace metals remaining in a reaction product.
One of the solutions to these problems of organometallic complexes is of supporting an organometallic complex to a solid support. Various solid-supported organometallic catalysts have been developed. Among these catalysts, activated charcoal, resins, or polymers or the like is commonly used as a solid support (see, for example, Non-Patent Documents 2 and 3). However, conventional solid-supported organometallic catalysts using these solid supports still leak trace amounts of metals from the supports. Further, in some solid-supported catalysts using resins or polymers as a solid support, a product and the like may be adsorbed on the solid support and thus the product may be difficult to be recovered efficiently. Now, in the field of solid-support catalyst, there is a demand for developing a solid support and a supporting method alternative to the conventional supports and methods. Under this circumstance, the present inventors have investigated to fix a catalyst metal more firmly by constructing a three-component structure of “semiconductor-sulfur-metal.” In other words, the present inventors have tried to develop a new catalyst having improved stability, leaking less amount of metals, and exhibiting reusable catalytic activity by modifying the surface of a substrate such as semiconductor, metal, or insulator with sulfur as a coupler and fixing an organometallic complex with the sulfur. As a result, the present inventors have found that a gallium arsenide (001) substrate modified with sulfur at the surface of the substrate can support an organometallic complex and that an amount of metals leaked from the organometallic complex is very smaller than that from an organometallic complex bonded to a conventional solid support in the Mizorogi-Heck reaction (see, for example, Patent Documents 1 to 3).